Synthesis of Novel Chiral Bicyclic Ligands and Their Application in Iridium-catalyzed Reactions

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ISBN 13 : 9789155462437
Total Pages : 72 pages
Book Rating : 4.4/5 (624 download)

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Book Synopsis Synthesis of Novel Chiral Bicyclic Ligands and Their Application in Iridium-catalyzed Reactions by : Anna Trifonova

Download or read book Synthesis of Novel Chiral Bicyclic Ligands and Their Application in Iridium-catalyzed Reactions written by Anna Trifonova and published by . This book was released on 2005 with total page 72 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Iridium Complexes in Organic Synthesis

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Publisher : John Wiley & Sons
ISBN 13 : 3527623086
Total Pages : 424 pages
Book Rating : 4.5/5 (276 download)

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Book Synopsis Iridium Complexes in Organic Synthesis by : Luis A. Oro

Download or read book Iridium Complexes in Organic Synthesis written by Luis A. Oro and published by John Wiley & Sons. This book was released on 2008-12-03 with total page 424 pages. Available in PDF, EPUB and Kindle. Book excerpt: Ranging from hydrogenation to hydroamination, cycloadditions and nanoparticles, this first handbook to comprehensively cover the topic of iridium in synthesis discusses the important advances in iridium-catalyzed reactions, namely the use of iridium complexes in enantioselective catalysis. A must for organic, complex and catalytic chemists, as well as those working with/on organometallics.

Synthesis and Application of Chiral Bicyclic Ligands in Assymetric Catalysis

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ISBN 13 :
Total Pages : 55 pages
Book Rating : 4.:/5 (185 download)

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Book Synopsis Synthesis and Application of Chiral Bicyclic Ligands in Assymetric Catalysis by : Jarle Sidney Diesen

Download or read book Synthesis and Application of Chiral Bicyclic Ligands in Assymetric Catalysis written by Jarle Sidney Diesen and published by . This book was released on 2005 with total page 55 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Chiral Ligands

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Publisher : CRC Press
ISBN 13 : 1000378985
Total Pages : 338 pages
Book Rating : 4.0/5 (3 download)

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Book Synopsis Chiral Ligands by : Montserrat Diéguez

Download or read book Chiral Ligands written by Montserrat Diéguez and published by CRC Press. This book was released on 2021-05-12 with total page 338 pages. Available in PDF, EPUB and Kindle. Book excerpt: Many new drugs on the market are chiral compounds, that is, they can exist in two non-superimposable mirror-image forms. Asymmetric catalysis encompasses a large variety of processes for obtaining such compounds. The performance of the catalyst in those processes largely depends on the ligand that makes up the catalyst. This book describes the most relevant ligand libraries for some key processes, including an overview of the state of art and the key mechanistic aspects that favor a high catalytic performance. Key Features: The book presents historical content from the time of discovery for each family of ligands. Provides a description of the synthetic route and the ligand library's application in various catalytic asymmetric reactions Suitable as supplementary reading for courses targeting the design, synthesis and application of chiral catalysts, asymmetric catalysis and sustainable production Edited by a distinguished scientist in the field, the book has a diverse audience including research groups in homogeneous catalysis, particularly asymmetric transformations

Studies Towards the Synthesis of Optically Active Bicyclo[2.2.2.]octa-2,5-dienes

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ISBN 13 :
Total Pages : 158 pages
Book Rating : 4.:/5 (826 download)

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Book Synopsis Studies Towards the Synthesis of Optically Active Bicyclo[2.2.2.]octa-2,5-dienes by : Breeyawn Nycole Lybbert

Download or read book Studies Towards the Synthesis of Optically Active Bicyclo[2.2.2.]octa-2,5-dienes written by Breeyawn Nycole Lybbert and published by . This book was released on 2012 with total page 158 pages. Available in PDF, EPUB and Kindle. Book excerpt: Optically active 2,5-disubstituted bicyclo[2.2.2]octa-2,5-dienes (bod) have found use within synthetic organic chemistry as chiral ligands for rhodium asymmetric catalysis reactions. These chiral ligands often provide greater enantioselectivity than their phosphorus-based chiral ligand cousins when employed in the formation of carbon-carbon bonds under rhodium catalysis. The drawback to using these types of 2,5-disubstituted bicyclo[2.2.2]octa-2,5-diene ligands is that they are very expensive to buy if they are commercially available or they must be synthesized if they are not commercially available. Present literature syntheses of these bod ligands rely on the physical separation of diastereomeric derivatives via recrystallization with low recovery or the separation of enantiomers via chiral HPLC, in which only small amounts of material may be separated. We have devised a synthesis of phenyl, benzyl, and methyl substituted bod ligands based on a bridged Robinson annulation reaction of 1,5-diketones and 1,5-ketoaldehydes, which gives the bicyclic core necessary for the bod ligand. Furthermore, our synthesis is designed to create optically active 1,5-diketones and 1,5-ketoaldehydes which transfer their chirality to the bicyclic core of the molecule. Our synthesis does not rely upon separation of racemic material at any step; instead we provide a method to synthesize any optically active bod ligand that is desired. We successfully synthesized the chiral 3-allylcyclohexanone (>95% ee), a key intermediate in our synthesis, using a chiral conjugate allylation of & alpha;, & beta;-unsaturated & beta;-ketoesters using Cu(OTf)2 and the chiral tBu-box ligand. We then successfully completed the racemic synthesis of 2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod) over 11 steps in 4.4% yield. The chiral Ph-bod ligand is projected to take 14 steps and proceed in a 1.1% overall yield. We also synthesized the racemic 2,5-bis(phenylmethyl)bicyclo[2.2.2]octa-2,5-diene (Bn-bod) over 7 steps in 1.4% overall yield. The synthesis of 2,5-dimethylbicyclo[2.2.2]ocat-2,5-diene (Me-bod) was attempted but was unsuccessful at this time. Ultimately we proved the utility of the bridged Robinson annulation reaction for the synthesis of various bicyclo[2.2.2]octa-2,5-dienes.

Privileged Chiral Ligands and Catalysts

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Publisher : John Wiley & Sons
ISBN 13 : 3527635211
Total Pages : 670 pages
Book Rating : 4.5/5 (276 download)

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Book Synopsis Privileged Chiral Ligands and Catalysts by : Qi-Lin Zhou

Download or read book Privileged Chiral Ligands and Catalysts written by Qi-Lin Zhou and published by John Wiley & Sons. This book was released on 2011-02-10 with total page 670 pages. Available in PDF, EPUB and Kindle. Book excerpt: Catalytic asymmetric synthesis has been one of the most active research areas in chemistry (Nobel Prize in 2001). The development of efficient chiral catalysts plays a crucial role in asymmetric catalysis. Although many chiral ligands/catalysts have been developed in the past decades, the most efficient catalysts are derived from a few core structures, called "privileged chiral catalysts". This ultimate "must have" and long awaited reference for every chemist working in the field of asymmetric catalysis starts with the core structure of the catalysts, explaining why a certain ligand or catalyst is so successful. It describes in detail the history, the basic structural characteristics, and the applications of these "privileged catalysts". This novel presentation provides readers with a much deeper insight into the topic and makes it a must-have for organic chemists, catalytic chemists, chemists working with/on organometallics, chemists in industry, and libraries. From the contents: * BINAP * Bisphosphacycles - From DuPhos and BPE to a Diverse Set of Broadly Applied Ligands * Josiphos Ligands: From Discovery to Technical Applications * Chiral Spiro Ligands * Chiral Bisoxazoline Ligands * PHOX Ligands * Chiral Salen Complexes * BINOL * TADDOLate Ligands * Cinchona Alkaloids * Proline Derivatives

Synthesis of Novel Chiral Dipyridylphosphine Ligands and Their Application in Ru- and Rh-catalyzed Asymmetric Hydrogenation Reactions

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Publisher :
ISBN 13 :
Total Pages : 722 pages
Book Rating : 4.:/5 (523 download)

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Book Synopsis Synthesis of Novel Chiral Dipyridylphosphine Ligands and Their Application in Ru- and Rh-catalyzed Asymmetric Hydrogenation Reactions by : Jing Wu

Download or read book Synthesis of Novel Chiral Dipyridylphosphine Ligands and Their Application in Ru- and Rh-catalyzed Asymmetric Hydrogenation Reactions written by Jing Wu and published by . This book was released on 2003 with total page 722 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Chiral Sulfur Ligands

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Publisher : Royal Society of Chemistry
ISBN 13 : 1847559247
Total Pages : 403 pages
Book Rating : 4.8/5 (475 download)

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Book Synopsis Chiral Sulfur Ligands by : Hélène Pellissier

Download or read book Chiral Sulfur Ligands written by Hélène Pellissier and published by Royal Society of Chemistry. This book was released on 2009 with total page 403 pages. Available in PDF, EPUB and Kindle. Book excerpt: The goal of this book is to show the high potential of chiral sulfur-containing ligands to promote numerous asymmetric catalytic transformations. These ligands can now be recognised as real competitors to the more usual phosphorus- or nitrogen-containing ligands.

Chiral Bisoxazoline Ligands in Catalytic Asymmetric Allylic Oxidation

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Publisher : LAP Lambert Academic Publishing
ISBN 13 : 9783838312507
Total Pages : 164 pages
Book Rating : 4.3/5 (125 download)

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Book Synopsis Chiral Bisoxazoline Ligands in Catalytic Asymmetric Allylic Oxidation by : Davoud Asgari

Download or read book Chiral Bisoxazoline Ligands in Catalytic Asymmetric Allylic Oxidation written by Davoud Asgari and published by LAP Lambert Academic Publishing. This book was released on 2009-09 with total page 164 pages. Available in PDF, EPUB and Kindle. Book excerpt: The Past three decades have witnessed a major development in asymmetric catalysis in organic synthesis. New and powerful catalysts have been designed and developed which exhibit levels of enantioselectivity previously considered beyond reach for non-enzymatic processes. Nitrogen-based transition metal ligands such as bisoxazoline ligands have emerged as an efficient class of ligands in an increasing number of asymmetric transformations including cyclopropanation, aziridination, Diels-Alder reaction, reduction, aldol reaction, ene reactions, allylic oxidation, and etc. This book reviews the synthesis and applications of bisoxazoline-metal complexes in a variety of asymmetric transformations and then describes the design and synthesis of a novel class of C2-symmetric biarylbisoxazoline ligands and their application in copper catalyzed asymmetric allylic oxidation of olefins. Potential applications for chiral cycloalkenols derived from allylic oxidation are great. A clear example is the conversion of (S)-cyclohexenyl benzoate to the key aldehyde-methyl ester intermediate for the synthesis of inflammation mediator leukotriene B4.

Synthesis of Novel Chiral Ligands for Catalytic Asymmetric Reactions

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ISBN 13 : 9789741438600
Total Pages : 640 pages
Book Rating : 4.4/5 (386 download)

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Book Synopsis Synthesis of Novel Chiral Ligands for Catalytic Asymmetric Reactions by :

Download or read book Synthesis of Novel Chiral Ligands for Catalytic Asymmetric Reactions written by and published by . This book was released on 2006 with total page 640 pages. Available in PDF, EPUB and Kindle. Book excerpt: A series of N-salicyl-beta-aminoalcohol ligands had been synthesized by three component Mannich type reaction followed by ring opening of oxazolidine derivatives with hydroxylamine hydrochloride. The reactions provided a series of chiral N-salicyl-beta-aminoalcohol ligands in high yields (84-92%) without any racemization. These synthesized compounds were evaluated as ligands for catalytic asymmetric Strecker reactions. N-Benzhydrylaldimines derived from aromatic and aliphatic aldehydes reacted withTMSCN in the presence of 10 mol% of Ti-ligand complex to give the alpha-aminonitriles in excellent yields and in up to >98% ee. In addition, the catalyst loading was successfully reduced to 2.5 mol% which is very effective and extremely simple for large scale synthesis. The presence of 2-propanol is essential to ensure good conversion and reaction rate. The absolute configuration of all products derived from the (S)-ligand was confirmed to be S. Racemization of alpha-aminophenylacetonitriles is catalyzed by weak acids such as silica (SiO[subscript 2]) or even methanol. However, the racemization can be suppressed by addition of either a base such as triethylamine (NEt[subscript 3]) or strong acid such as hydrochloric acid (HCI). Importantly, optically active alpha-aminoacetonitriles can be easily converted to arylglycines by complete hydrolysis with minimal racemization. (>80% and >90% ee). A transition state model to explain the enantioselectivity of the reaction is proposed. The present chiral catalysts showed their catalytic ability in not only asymmetric strecker reaction but also asymmetric Pudovic reaction as well as asymmetric Michael addition.

Design and Synthesis of Novel Chiral Bisoxazoline Ligands for the Catalytic Asymmetric Allylic Oxidation

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Publisher :
ISBN 13 :
Total Pages : 150 pages
Book Rating : 4.:/5 (516 download)

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Book Synopsis Design and Synthesis of Novel Chiral Bisoxazoline Ligands for the Catalytic Asymmetric Allylic Oxidation by : Davoud Asgari

Download or read book Design and Synthesis of Novel Chiral Bisoxazoline Ligands for the Catalytic Asymmetric Allylic Oxidation written by Davoud Asgari and published by . This book was released on 2001 with total page 150 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Synthesis of New Chiral Ligands and Their Application in Catalytic Enantioselective Reactions

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Publisher :
ISBN 13 :
Total Pages : 131 pages
Book Rating : 4.:/5 (838 download)

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Book Synopsis Synthesis of New Chiral Ligands and Their Application in Catalytic Enantioselective Reactions by : Kedar Shankar Karmarkar

Download or read book Synthesis of New Chiral Ligands and Their Application in Catalytic Enantioselective Reactions written by Kedar Shankar Karmarkar and published by . This book was released on 1996 with total page 131 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Artificial Metalloenzymes and MetalloDNAzymes in Catalysis

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Publisher : John Wiley & Sons
ISBN 13 : 3527804072
Total Pages : 431 pages
Book Rating : 4.5/5 (278 download)

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Book Synopsis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis by : Montserrat Diéguez

Download or read book Artificial Metalloenzymes and MetalloDNAzymes in Catalysis written by Montserrat Diéguez and published by John Wiley & Sons. This book was released on 2018-02-21 with total page 431 pages. Available in PDF, EPUB and Kindle. Book excerpt: An important reference for researchers in the field of metal-enzyme hybrid catalysis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a comprehensive review of the most current strategies, developed over recent decades, for the design, synthesis, and optimization of these hybrid catalysts as well as material about their application. The contributors—noted experts in the field—present information on the preparation, characterization, and optimization of artificial metalloenzymes in a timely and authoritative manner. The authors present a thorough examination of this interesting new platform for catalysis that combines the excellent selective recognition/binding properties of enzymes with transition metal catalysts. The text includes information on the various applications of metal-enzyme hybrid catalysts for novel reactions, offers insights into the latest advances in the field, and contains an informative perspective on the future: Explores the development of artificial metalloenzymes, the modern and strongly evolving research field on the verge of industrial application Contains a comprehensive reference to the research area of metal-enzyme hybrid catalysis that has experienced tremendous growth in recent years Includes contributions from leading researchers in the field Shows how this new catalysis combines the selective recognition/binding properties of enzymes with transition metal catalysts Written for catalytic chemists, bioinorganic chemists, biochemists, and organic chemists, Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a unique reference to the fundamentals, concepts, applications, and the most recent developments for more efficient and sustainable synthesis.

Development of Metal-alkynylide Additions to Imines, Iminiums and Epoxides

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ISBN 13 :
Total Pages : 0 pages
Book Rating : 4.:/5 (847 download)

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Book Synopsis Development of Metal-alkynylide Additions to Imines, Iminiums and Epoxides by : Christian Fischer

Download or read book Development of Metal-alkynylide Additions to Imines, Iminiums and Epoxides written by Christian Fischer and published by . This book was released on 2004 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:

The Synthesis and Application of Bulky S-stereogenic and P- Stereogenic Chiral Ligands

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ISBN 13 :
Total Pages : 305 pages
Book Rating : 4.:/5 (892 download)

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Book Synopsis The Synthesis and Application of Bulky S-stereogenic and P- Stereogenic Chiral Ligands by : Seán Doran

Download or read book The Synthesis and Application of Bulky S-stereogenic and P- Stereogenic Chiral Ligands written by Seán Doran and published by . This book was released on 2012 with total page 305 pages. Available in PDF, EPUB and Kindle. Book excerpt: This doctoral thesis was focused on the design and synthesis of novel chiral ligands for application in asymmetric catalysis. One of the best examples of asymmetric catalysis is the asymmetric hydrogenation reaction for its atom economy, ease of access to both S and R enantiomers and almost ultimate enantiomeric excess obtainable in a multitude of substrates. There has been much investigation into this reaction and there has been a plethora of chiral ligands designed which catalyze this reaction in high enantiomeric excess using metals such as rhodium, iridium and ruthenium. The vast majority of these ligands are diphosphines with their chirality lying either on the backbone of the ligand or on the coordinating phosphorus atom itself. In the beginning of this work investigation was undertook to explore the possibility of successfully employing a new type of ligand class in the asymmetric hydrogenation reaction, namely the N-phosphino sulfinamide or PNSO ligands. PNSO ligands had been successfully applied to the asymmetric Pauson-Khand reaction in the Riera group yielding cyclopentenone Pauson-Khand adducts in high yield and very high enantioselectivity. The family of PNSO ligands prepared in the Riera group was attractive because apart from the high yields and enantioselectivities obtained from the reactions in which they were used, they proved to be easily prepared in short syntheses from commercially available starting materials. It was believed if they could be successfully applied in asymmetric hydrogenation for their ease of preparation they would be an attractive alternative to the diphosphine ligand class. Unfortunately the first two PNSO-Rh complexes successfully prepared provided low enantioselectivities and difficulties were encountered while trying to prepare further analogues. After some time trying to achieve PNSO-Rh complex analogues unsuccessfully the direction of the project was shifted away from the N-phosphino sulfinamide ligand class in asymmetric hydrogenation. The MaxPhos ligand had recently been developed in the group and had proven highly promising. A study was demanded of its substrate scope as applied in rhodium catalyzed asymmetric hydrogenation. Substrates already described in the literature were prepared and the asymmetric hydrogenation of them catalyzed by the MaxPhos-Rh precatalyst was performed and conditions to do so were optimized. Of seven substrates prepared the MaxPhos-Rh proved to hydrogenate five of those with high enantioselectivity. The TOF of the MaxPhos rhodium catalyst applied in the hydrogenation of the Z-MAC substrate was examined by monitoring the flux of hydrogen and was calculated at 0.065 s-1. MaxPhos complexes of cobalt and palladium were prepared to form part of the investigation into widening the reaction scope of the ligand. [(MaxPhos)Co2(CO)4(C2H2)] proved to catalyze the Pauson-Khand reaction of norbornadiene and 1-hexyne with 24 % yield and 28 %, a noteworthy enantiomeric excess for the catalytic asymmetric Pauson-Khand reaction. Chalcogenated derivatives of MaxPhos were prepared. The diselenide was used to explore the electronic nature of the ligand. The MaxPhos-rhodium carbonyl stretching was examined. MaxPhos-BH3 was used to prepare mono-chalcogenated MaxPhos derivatives. They were applied also in asymmetric hydrogenation once complexed to rhodium but enantiomeric excess of no more than 21 % was obtained in the hydrogenation of the substrate Z-MAC. The aminophosphine, a chiral building block and key intermediate in the preparation of the MaxPhos ligand, was used in the attempt to prepare bulky chiral amidine ligands and although two such species were prepared they proved inapplicable in asymmetric catalysis.

Ligand Platforms in Homogenous Catalytic Reactions with Metals

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Publisher : John Wiley & Sons
ISBN 13 : 1118943090
Total Pages : 358 pages
Book Rating : 4.1/5 (189 download)

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Book Synopsis Ligand Platforms in Homogenous Catalytic Reactions with Metals by : Ryohei Yamaguchi

Download or read book Ligand Platforms in Homogenous Catalytic Reactions with Metals written by Ryohei Yamaguchi and published by John Wiley & Sons. This book was released on 2014-10-15 with total page 358 pages. Available in PDF, EPUB and Kindle. Book excerpt: Serving as a user's manual for synthetic organic and catalytic chemists, this book guides chemists in the design and choice of ligands to catalyze organic reactions and apply the results for more efficient, green, and practical synthesis. • Focuses on the role of ligands in metal complexes that catalyze green organic transformations: a hot topic in the area of organic synthesis and green chemistry • Offers a comprehensive resource to help readers design and choose ligands and understand selectivity/reactivity characteristics • Addresses a gap by taking novel ligand approaches and including up-to-date discussion on hydrogen transfers and reactions • Presents important industrial perspective and provides rational explanations of ligand effects, impacts, and novelty

Synthesis and Application of New Chiral Ligands for Enantioselectivity Tuning in Transition Metal Catalysis

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Publisher :
ISBN 13 :
Total Pages : 156 pages
Book Rating : 4.:/5 (13 download)

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Book Synopsis Synthesis and Application of New Chiral Ligands for Enantioselectivity Tuning in Transition Metal Catalysis by : Fanji Kong

Download or read book Synthesis and Application of New Chiral Ligands for Enantioselectivity Tuning in Transition Metal Catalysis written by Fanji Kong and published by . This book was released on 2017 with total page 156 pages. Available in PDF, EPUB and Kindle. Book excerpt: A set of five new C3-symmetric phosphites were synthesized and tested in palladium-catalyzed asymmetric Suzuki coupling. The observed reactivity and selectivity were dependent upon several factors. One of the phosphites was able to achieve some of the highest levels of enantioselectivity in asymmetric Suzuki couplings with specific substrates. Different hypotheses have been made for understanding the ligand effects and reaction selectivities, and those hypotheses were tested via various methods including DOSY NMR experiments, X-ray crystallography, and correlation of catalyst selectivity with Tolman cone angles. Although only modest enantioselectivities were observed in most reactions, the ability to synthesis these phosphites in only three steps on gram scales and to readily tune their properties by simple modification of the binaphthyl 2́-substituents makes them promising candidates for determining structure-selectivity relationships in asymmetric transition metal catalysis, in which phosphites have been previously shown to be successful. A series of novel chiral oxazoline-based carbodicarbene ligands was targeted for synthesis. Unfortunately, the chosen synthetic route could not be completed due to unwanted reactivity of the oxazoline ring. However, a new and efficient route for Pd-catalyzed direct amination of aryl halides with oxazoline amine was developed and optimized during these studies. Chiral binaphthyl based Pd(II) ADC complexes with different substituent groups have been synthesized and tested in asymmetric Suzuki coupling reactions. Although only low enantioselectivities were observed in Suzuki coupling, this represents a new class of chiral metal-ADC catalysts that could be tested in further catalytic.